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| CAS No.: | 605-65-2 |
|---|---|
| Name: | Dansyl chloride |
| Molecular Structure: | |
|
|
|
| Formula: | C12H12ClNO2S |
| Molecular Weight: | 269.752 |
| Synonyms: | 1-(Dimethylamino)-5-naphthalenesulfonylchloride;5-(Dimethylamino)-1-naphthalenesulfonyl chloride;5-(N,N-Dimethylamino)-1-naphthalenesulfonylchloride;DNS chloride;NSC 83616; |
| EINECS: | 210-092-6 |
| Density: | 1.361 g/cm3 |
| Melting Point: | 70-73 °C(lit.) |
| Boiling Point: | 371.3 °C at 760 mmHg |
| Flash Point: | 178.4 °C |
| Solubility: | Soluble in dimethyl fluoride, acetone, chloroform, pyridine, benzene and dioxane. Insoluble in water. |
| Appearance: | yellow to orange-yellow crystalline powder |
| Hazard Symbols: |
 C
|
| Risk Codes: | 34 |
| Safety: | 26-36/37/39-45-3 |
| Transport Information: | UN 3261 8/PG 2 |
| PSA: | 45.76000 |
| LogP: | 3.91410 |
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Chemistry
Molecular Formula: C12H12ClNO2S
Molar mass: 269.75g/mol
EINECS: 210-092-6
Melting point: 70-73 °C
Density: 1.361 g/cm3
Flash Point: 178.4 °C
Index of Refraction: 1.636
Boiling Point: 371.3 °C at 760 mmHg
Vapour Pressure: 1.04E-05 mmHg at 25°C
Structure of Dansyl chloride (CAS NO.605-65-2):
Systematic Name: 5-Dimethylaminonaphthalene-1-sulfonyl chloride
SMILES: ClS(=O)(=O)c1cccc2c1cccc2N(C)C
InChI: InChI=1/C12H12ClNO2S/c1-14(2)11-7-3-6-10-9(11)5-4-8-12(10)17(13,15)16/h3-8H,1-2H3
InChIKey: XPDXVDYUQZHFPV-UHFFFAOYAI
Std. InChI: InChI=1S/C12H12ClNO2S/c1-14(2)11-7-3-6-10-9(11)5-4-8-12(10)17(13,15)16/h3-8H,1-2H3
Std. InChIKey: XPDXVDYUQZHFPV-UHFFFAOYSA-N
Uses
Dansyl chloride (CAS NO.605-65-2) is widely used to modify amino acids; specifically, protein sequencing and amino acid analysis, and may also be denoted DNSC.
Production
5-(Dimethylamino)-1-naphthalenesulfonyl chloride (CAS NO.605-65-2) may be prepared by reacting the corresponding acid with excess Phosphorus oxychloride (POCl3) at room temperature.
Toxicity Data With Reference
| 1. | ivn-mus LD50:56 mg/kg | CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#00262 . |
Consensus Reports
Reported in EPA TSCA Inventory.
Safety Profile
Poison by intravenous route. When heated to decomposition it emits very toxic fumes of Cl− and NOx.
Hazard Codes: C.gif){kind=small}
Risk Statements:
34: Causes burns
Safety Statements:
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
37: Wear suitable gloves
39: Wear eye/face protection
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
Specification
Dansyl chloride (CAS NO.605-65-2) also can be called 1-Chlorosulfonyl-5-(dimethylamino)naphthalene ; 1-Naphthalenesulfonyl chloride, 5-(dimethylamino)- ; and 1-(Dimethylamino)-5-naphthalenesulfonyl chloride . It is a reagent that reacts with primary amino groups in both aliphatic and aromatic amines to produce stable blue- or blue-green–fluorescent sulfonamide adducts.Likewise, a similar derivative, it is known as DNSA.In addition, these protein-DNSC conjugates are sensitive to their immediate environment. 5-(Dimethylamino)-1-naphthalenesulfonyl chloride is unstable in dimethyl sulfoxide, which should never be used to prepare solutions of the reagent.The extinction coefficient of dansyl derivatives are important for measuring their concentration in solution.For all of the studies, the absorption value is always taken at the maximum that appears between 310 nm and 350 nm.